Multicomponent Synthesis of Spiroisoxazolines

Adamo, Mauro F. A.; Donati, Donato; Duffy, Eleanor F.; Sarti‐Fantoni, P.

doi:10.1021/jo051181w

Cited by 70 publications

(31 citation statements)

References 19 publications

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“…Compounds MA04 (Scheme 4) were obtained by reacting equimolar amounts of 3,5-dimethyl-4-nitroisoxazole (Isi), an aromatic aldehyde (Ald) and a -diketone (K) in the presence of substoichiometric amounts of piperidine base. 8 Compounds MA05…”

Section: Synthesis Of Scaffolds Ma01-ma21mentioning

confidence: 99%

“…8 This study generated several one-pot multicomponent reactions, the synthetic details of which were described in previous papers. [8][9][10][11][12][13] Diversity is achieved by substituting each of three or four substituents at one time and keeping the synthetic strategy already optimized constant. In this fashion synthesis of opportunely modified structures could be achieved within hours/days instead of weeks/months.…”

Section: Introductionmentioning

confidence: 99%

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TIN − A Combinatorial Compound Collection of Synthetically Feasible Multicomponent Synthesis Products

Dorschner

Toomey

Brennan

et al. 2011

J. Chem. Inf. Model.

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• to copy, distribute, display, and perform the work.• to make derivative works. Under the following conditions:• Attribution -You must give the original author credit.• Non-Commercial -You may not use this work for commercial purposes.• Share Alike -If you alter, transform, or build upon this work, you may distribute the resulting work only under a licence identical to this one. For any reuse or distribution, you must make clear to others the licence terms of this work. Any of these conditions can be waived if you get permission from the author. Your fair use and other rights are in no way affected by the above. The synthetic feasibility of any compound library used for virtual screening is critical to the drug discovery process. TIN, a recursive acronym for "TIN Is Not commercial", is a virtual combinatorial database enumeration of diversity-orientated multicomponent syntheses (MCR). Using a "one-pot" synthetic technique, 12 unique small molecule scaffolds were developed, predominantly styrylisoxazoles and bis-acetylenic ketones, with extensive derivatization potential. Importantly, the scaffolds were accessible in a single operation from commercially available sources containing R-groups which were then linked combinatorially. This resulted in a combinatorial database of over 28 million product structures, each of which is synthetically feasible. These structures can be accessed through a free webbased 2D structure search engine, or download in SMILES, MOL2 and SDF formats. Subsets include a 10% diversity subset, a drug-like subset and a lead-like subset that are also freely available for download and virtual screening (http://mmg.rcsi.ie:8080/tin).

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Section: Synthesis Of Scaffolds Ma01-ma21mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

TIN − A Combinatorial Compound Collection of Synthetically Feasible Multicomponent Synthesis Products

Dorschner

Toomey

Brennan

et al. 2011

J. Chem. Inf. Model.

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“…3-Methyl-4-Nitro-5-styrylisoxazoles 1 [1][2][3][4][5][6][7][8][9] and 2 [3] (Scheme 1) represent two types of polyfunctional scaffold which hold excellent potential for the generation of diversity ( Figure 1) [1][2][3][4][5][6][7][8][9]. Compounds 1 and 2 can be readily prepared from commercially available 3,5-dimethyl-4-nitroisoxazole 3 and aromatic aldehydes 4 ( Figure 1) [10].…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, compounds 1 have two electrophilic centers that can be selectively reacted. Enolates, which are stabilized soft nucleophiles, react at the soft electrophilic center E2, whereas hard nucleophiles such as hydroxide react exclusively at the hard electrophilic center E1 ( Figure 1) [1][2][3][4][5][6][7][8][9][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Cyclopropanation of 5-(1-Bromo-2-phenyl-vinyl)-3-methyl-4-nitro-isoxazoles under Phase Transfer Catalysis (PTC) Conditions

et al. 2015

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“…1 Following the first reports of their herbicidal and plant hormonal activity [2][3][4] some naturally occurring spiroisoxazolines have been found useful in other biomedical areas.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of chiral NiII complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid

Micuch¹,

Fišera²,

Kožı́šek³

et al. 2006

Arkivoc

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The chiral Ni II complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid (6) was prepared via the cycloaddition of chiral complex of Ni 5 with mesitonitrile oxide 1. The cycloaddition proceeded with complete regioselectivity to provide 5-substituted isoxazolines 6 and 7. The approach of the dipole takes place predominantly from the less sterically hindered side of dipolarophile 5, the diastereoisomers were formed in 96:4 ratio. The detailed structure of 6 was established by X-ray analysis.

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Multicomponent Synthesis of Spiroisoxazolines

Abstract: A three-component one-pot procedure (3-MCR) was developed to assemble the spiroisoxazoline nucleus from commercially available materials. This new methodology affords the title compounds in high yields and without the use of chromatography.

Cited by 70 publications

References 19 publications

TIN − A Combinatorial Compound Collection of Synthetically Feasible Multicomponent Synthesis Products

TIN − A Combinatorial Compound Collection of Synthetically Feasible Multicomponent Synthesis Products

Cyclopropanation of 5-(1-Bromo-2-phenyl-vinyl)-3-methyl-4-nitro-isoxazoles under Phase Transfer Catalysis (PTC) Conditions

The synthesis of chiral NiII complex of Schiff base of (S)-2-N-(N-benzylprolyl)aminobenzophenone and 5-amino-4,5-dihydro-3-(2,4,6-trimethylphenyl)isoxazol-5-carboxylic acid

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